Leadership · Mastering Positive Attitude Habits · Personal Competencies

5 Tips: Working Productively with Challenging People

They seem to be everywhere. They are labeled, “Difficult People”. Working with Difficult People is one of the most common training topic requests I receive and my recent workshop quickly had an overflow list of registrants. How can you work productively with challenging people? What if YOU are the challenging person? Listen and gain information and tools you can apply immediately to work in your highest potential and improve your job satisfaction level.


The Relatable Leader podcast and my blog are sponsored by my book, “LIVE IT! Mastering Positive Attitude Habits, 15 Tips For Managing Your Mindset.” Those tips include Practice Tenacity and Be Resourceful, both of which have been central to my career. Get the book on Amazon and start working on those action assignments now, moving closer and closer to your goals through small wins every day! Get the book here:


Things have been busy on the training front. My workshop, “Working Productively with Challenging People,” had an overflow list of participants register, so we added a second session. In the workshop I provide a rating sheet I refer to as Myers Briggs lite, and once participants complete the rating sheet, I provide an answer key with specific tips for how to flex to other styles. Other styles often correlate to the people that are challenging to you. Turns out it was a popular subject for others as well. I noticed Oprah’s magazine ran an article last week written by M. J. Ryan, also about working with difficult people. He offers five tips on the subject:

  1. Don’t push buttons that don’t need to be pushed. Exactly! One of my training participants let me know he’s been thinking a lot about one of my rules for reducing conflict: if no good will come of it, don’t do it or say it! I understand the need to tell people what we think, but if you say it THAT way…you know what way I’m talking about…no good will come of it. People tell me, “But I was RIGHT!” Yes, you were right, and now you are alone or fired, so was it worth it? Learn how to get your point across without pushing people’s buttons.


  1. Presume goodwill. This can be tough when people have a proven track record of being self-serving jerks. In my working with challenging people workshop, I talk about the importance of opening the possibility for people to be different. If your voice, word choice, and body language predict the actions of a self-serving jerk or apathetic coworker, then that’s what will be reflected back to you. If you put up your defenses prepared for an attack of some type, the other person will feel that and likely respond accordingly. If you believe someone is out to get you, that’s what you will see. SOMEONE has to break the cycle. If you have the emotional maturity to modify your behaviors to open up the possibility of a different way of being – of interacting – then MAYBE the other person’s goodwill will shine through. Maybe not. But you can end the work day knowing you changed your behaviors to give the other person an option to meet you in that place.


  1. Remember your intention. Yep. Knowing your intention and communicating in a way that accurately represents your intention is central to my communication series. What words most closely represent your intended meaning? What tone of voice and facial expression can you demonstrate to match your words? In my experience, it takes a lot of discipline to maintain focus on your intention when the other person seems oblivious or ignores what you are saying completely. Since all we can control is our own behaviors, sometimes your only win in these situations is knowing you did your best with a difficult coworker. But every now and then, the person will hear and see your intentions and they will make the effort to change their behaviors too. That’s fantastic, so rewarding, even if the outcome is not exactly what you were hoping for. In this way you are training your coworkers, no matter what role you fill.


  1. Argue for their side. Hummm, interesting. That’s not a tip I typically recommend, so it got my attention. I recommend trying to see the situation from the other person’s point of view, but this tip takes it to the next level. In the typical situations clients describe to me, arguing the other point of view might sound like this:


  1. “I think one could argue that you don’t have time to do this correctly in addition to all the other things people in your role are expected to do. Since Mary is able to meet the requirements of this role, I took a deeper look into her work history. I noticed she had five years’ experience at so and so company doing such and such type of work. Maybe, for future hires, we need to modify our post and require five years’ experience doing this type of work. What do you think?….How can we support your success in this role? I’m wondering if we owe it to you to provide additional training in the area where you are struggling – what do you think?”
  2. Another example: “You’re right, it seems like they don’t care about us. I think there is a clear expectation of people being hired who can do their jobs and problem solve when challenges arise. It seems like they expect us to handle our jobs without them having to check in with us to find out what is going on and how it affects us. Tell me about your previous work experiences – have you had leadership that checked in with you the way you think they should? If so, where was it? What kind of work were you doing?”

I’m going to keep thinking about M.J. Ryan’s tip to argue for the other side, and look for opportunities to practice it. If I have positive results using this technique, I’ll let you know.

  1. I’m going to modify the language on this tip to match the content from my training. This is what I say: “You’re always having an impact. The question is, does the impact you are actually having match the impact you want or hope to have?” One of the biggest interpersonal struggles I observe in people is they don’t pay attention to the impact of their actions. They offend, insult, demean, hurt, or confuse others, and they remain clueless. Then they wonder why they never get promoted or why they feel left out. Because it’s challenging to work with you! Pay attention and figure it out! It sounds basic, but it doesn’t come naturally to many: think before you talk. Think before you act. Identify your goal and communicate in a way that supports your goal. Focus more on contributing to your work team than taking from your work team. How can you collaborate instead of constantly focusing on how everything impacts YOU? I think front line workers naturally focus on how most things impact them. In leadership, we must focus on a tiered perspective: how does everything impact our customers? How does this impact our organization? How does this impact my team?

Hear the podcast episode based on this article:

5 Tips For Working Productively with Challenging People

Remember, we want people to judge us based on our intentions. However, we are instead judged by what we are actually saying and doing.

Above average: be the person who considers a person’s intentions, even while judging their behaviors.

May I invite you to please go to my website, Relatableleader.com and click on the link at the top of the page to complete the 10-question conflict survey?  I’m collecting data for my next book and I appreciate your contribution to this effort. Thank you!




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